Cellulosic composition of matter containing acetyl phenyl glycine



Patented Dot. 6, 1931 UNITED STATES PATENT oF lcs -g STEWARTJ. CARROLL, or ROCHESTER, NEW YORK, ASSIGNOR T EAs'rMAN'xonAx COMPANY, or ROCHESTER, new YORK, A CORPORATION or NEW YORK CELLULOSIC COMPOSITION OF MATTER CONTAINING ACETYLPHENYL GLYCINE Application filed. August 30, 1929. Serial No. 389,449.

. This invention relates to compositions of matter in which cellulose derivatives, such as cellulose acetate, cellulose nitrate or cellulose ether, are combined or mixed with other a substances, such as a compatible plasticizer,

and a common solvent for both, with or without other useful addition agents, so that the resulting product will have properties such as will make the composition highly advantageous for use in the plastic and analogous arts, such, for instance, as the manufacture of wrapping sheets, photographic films, artificial silk, varnishes orlacquers, and the like. One object of this invention is to produce a composition of matter which may be made into permanently transparent, strong and :fiex bile sheets or films of desired thinness which are substantially waterproof, are unaffected by ordinary photographic fluids and -possess the desired properties of asupport for sensitive photographic coatings. An-

other ,object of my invention is to produce a composition which is capable of easy and convenient manipulation in the plastic and anali ogous arts, such as in the manufacture of sheets, films, artificial silk filaments, varnishes, lacquers and the like and to produce 1 a composition which will not injure, or be injured by, the substances or surface-s with which it is associated .during manufacture, storage or use. Other and further objects will hereinafter become apparent to those skilled in the art to which this invention pertains.

While cellulose acetates, nitrates and others have been known for decades it has also been known that to utilize them in the various plastic arts it is necessaryto mix therewith such plasticizing or conditioning agents as.

camphor, castor oil, triphenyl phosphate, "monochlornaphthalene or the like. Certain of these and other addition agents are also added for the purpose of reducing the inflammability of the product. Plastic inductheir esters, are sometimes also added. Similarly addition compounds of various kinds have been employed, to increase flexibility, transparency, toughness and other properties whichrwill enhance the value of the reing agents, such as the higher alcohols and sulting product. Addition products for the same or similar purposes are also added to cellulose acetates, nitrates and ethers to prepare them for use in the other plastic arts, such as in the manufacture of lacquers, varnishes, artificial silk filaments, moulded compounds and the'like. While the plasticizers or other addition agents heretofore discovered have had their utility in the art, the increasing use to which cellulose derivatives have been put and the increasing number of desirable properties required of the cellulose derivative for'most purposes has made the discovery of new and economical plasticizers or other addition agents a matter of considerable importanceto the art. i

I'have discovered that valuable properties may be induced in and/orcontributed to compositions containing cellulose derivatives, such as cellulose acetate, by adding vthereto the plasticizing compound acetyl-phenyl gly-v cine in the presence of a solvent, such as acetone, whichwill dissolve both the cellulose derivative and plasticizer. This plasticizer is a solid at ordinary atmospheric temperature and has'the structural formula of i It is compatible with cellulose derivatives and particularly compatible with cellulose acetate in the percentages hereinafter given. Itis The particularly useful proptone soluble cellulose acetate i. 'e." cellulose 1 acetate containing from 36% to 42% acetyl radical, approximately, is dissolved with stirring at atmospheric temperature in 300 to 500 parts, preferably 400 parts, by weight, of acetone. To this solution may be added from 10 to 50 parts by weight, of acetylphenyl glycine, it being found preferable to employ approximately parts thereof. WVithin the limits stated, the amount of plasticizer may be decreased or increased, de-

pending upon whether it is desired to decrease or increase, respectively, the properties which this plasticizer contributes to the finished product. The amount of solvent employed may also be decreased or increased, depending upon whether it is desired to have a more or less freely flowing composition, respectively.

A composition of matter prepared as above described may be deposited upon any suitable film forming surface to form a film or sheet, as is well known to those skilled in the art. A film so produced has permanently brilliant transparency and low infiammability, burning no more readily than ordinary newsprint. Such film is tought and flexible as shown by the fact that it will withstand many folds upon a modified Sehopper fold-tester (commonly used for such purposes) without breaking and that even after being subjected for 114 days to air maintained at a temperature of 65 C. the film still maintains flexibility, demonstrating that the film will withstand ordinary usage satisfactorily for many years, whereas a film formed from a mere solution of cellulose acetate in acetone or other similar solvent is brittle and fragile after being subjected to the same treatment for as little as thirty days or even a lesser time. The sum total of the above advantageous propertiesof a product produced from my new composition is considerably in excess of that of products produced with what have previously been regarded as the better plasticizers.

Other similar solvents (instead of acetone) which are compatible with the cellulose acetate and my new plasticizer may also occur to those skilledin this art. In like manner this plasticizer may be compound-ed with other single organic esters of cellulose, such as cellulose propionate, butyrate and the like, or with mixed organic and/ or inorganic esters, such as cellulose aceto-stearate, acetomalate, or cellulose nitro-acetate, or with the cellulose ethers, a suitable solvent which will dissolve both the cellulosic derivative and the plasticizer being employed.

The accompanying drawing, forming a part of this application, clearly illustrates the particular advantages of employing my novel plasticizer in the plastic arts. In this drawing there are plotted lines or curves graphically depicting the properties of film produced from a composition containing cel lu-lose acetate and this plasticizer. On the horizontal axis is indicated the various perteases? centages of my plasticizer that may be employed with the cellulosic derivative, this percentage being given in parts added to the cellulose derivative rather than parts of the composition; for instance, 30 parts plasticizer added to parts cellulose acetate is denoted as 30% plasticizer added. On the vertical axis at (a), on the left, is indicated in percentage over the check sample the initial flexibility of a film which has been formed as described from my novel composition and which has been subjected to air at 50 C. for 94 hours to free it of solvent;

the rate of combustion of that film is also,

indicated by this same column (a); at on the right is indicated the length of time in days that the film will maintain flexibility *hen subjected to air kept atemperature of 65 C. The curve (A) depicts initial flexibility of the film, the curve (B) depicts the ability of the film to maintain flexibility and the curve (C) depicts the rate of combustion of the film-all with various percentages of my novel nlasticizer and all as compared to the respective properties of a film produced from a solution of cellulose acetate in acetone and a hypothetical inert material substitutd for the plasticizer as denoted by curve (1)) indicating unity of 100% and 30 days for (a) and (b). It will thus be noted that my novel plasticizer has the faculty of giving, to a product produced therefrom, good initial flexibility and a low combustion rate, and that the product maintains its flexibility exceptionally well. The preferred percentage of my plasticizer which it is desirable to employ to contribute a; y particular property to the final productwill be obvious from an inspection of this drawing; the best percentage to employ will depend upon which property it is desired to feature most in the final product.

lnasmuch as my above described composition of matter is quite useful in the production of films and sheets it will be apparent that my new plasticizer may also be employed with advantage in the other branches of the plastic art. For instance, my above described composition of matter may be employed in the manufacture of artificial silk by the dry spinning method. lVith the proper coagulating bath it may also be employed for wet spinnin It may be desired to employ a composition of different viscosity or evaporation characteristics but this is a mere matter of changing the solvent proportion or tage in connection with a number of the known lacquer and varnish formulae with which it may be found to be compatible. In

such cases the plasticizer is usually first put What I claim as my invention, and desire to be secured by Letters Patent of the United States, is:

1. A composition of matter comprising a cellulose derivative and acetyl-phenyl glycine.

2. A composition of matter comprising cellulose acetate and acetyl-phenyl glycine. 3. A'composition of matter comprising 100 parts cellulose acetate and from about 10 to 50 parts, by Weight, of acetyl-phenyl glycine.

4. A composition of matter comprlsing 100.

parts of cellulose acetate and approximately 30 parts, by Weight, of acetyl-phenyl glycine. Signed at Rochester, New York this 27th day of August 1929. V

. STEWART J. CARROLL. 

